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Eastern Europe

Moshe Teitelbaum

Here we see another black velvet kippah, this one from the 18th Century.  So the modern-style kippah doesn't seem so much "modern" as "regional."  Although it doesn't surprise me that this ended up being the predominant style in America two hundred years later; this is where most American Jews came from.

Shneur Zalman of Liadi

Interestingly, the oldest picture of a 19th Century Russian rabbi shows a very simple, modern-looking black velvet kippah. I was calling this "modern" when I saw an Uzbeki rabbi wearing it (see above), but maybe this was a regional thing instead.